Li, Guang’s team published research in Chemical Engineering Journal (Amsterdam, Netherlands) in 433 | CAS: 826-36-8

Chemical Engineering Journal (Amsterdam, Netherlands) published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, Recommanded Product: 2,2,6,6-Tetramethylpiperidin-4-one.

Li, Guang published the artcileFe3O4 supported on water caltrop-derived biochar toward peroxymonosulfate activation for urea degradation: the key role of sulfate radical, Recommanded Product: 2,2,6,6-Tetramethylpiperidin-4-one, the publication is Chemical Engineering Journal (Amsterdam, Netherlands) (2022), 433(Part_2), 133595, database is CAplus.

A new type of iron-doped and porous biochar (Fe@BC) derived from water caltrop was systematically investigated to catalyze the organic pollutants degradation by peroxymonosulfate (PMS). The effectiveness of this novel material was tested by treating excessive urea concentrations in swimming pool water. It exhibited good PMS activation capacity, achieving urea removal of 100% within 15 min. The Fe@BC/PMS system exhibited excellent resistance to common anions. Only chloride showed a small inhibitory effect, and the removal efficiency of urea decreased by 10% ([Cl]0 = 10 mM). Quenching experiments and ESR spectroscopy analyses demonstrated that urea degradation was mainly mediated by the radical pathway, which in turn was dominated by surface-bound sulfate radicals (SO4·-). Further, reusability experiments confirmed the stability of the material. After three cycles, the degradation efficiency can still reach 86%. Therefore, the conversion of water caltrop-derived biochar into a composite catalytic material provides a novel strategy for value-added utilization of aquatic waste biomass, and it is also a promising alternative for the treatment of urea from swimming pool water.

Chemical Engineering Journal (Amsterdam, Netherlands) published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, Recommanded Product: 2,2,6,6-Tetramethylpiperidin-4-one.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

 

Wu, Wenjie’s team published research in ACS Applied Materials & Interfaces in 13 | CAS: 826-36-8

ACS Applied Materials & Interfaces published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C15H20O6, Product Details of C9H17NO.

Wu, Wenjie published the artcileDefect-Engineered Graphene Films as Ozonation Catalysts for the Devastation of Sulfamethoxazole: Insights into the Active Sites and Oxidation Mechanism, Product Details of C9H17NO, the publication is ACS Applied Materials & Interfaces (2021), 13(44), 52706-52716, database is CAplus and MEDLINE.

Graphene-based catalysts have been widely applied for catalytic ozonation. However, as it is difficult to obtain graphene with high structural precision, it is currently unfeasible to comprehend the relationships between the intrinsic structure of the layered carbon catalysts with its catalytic activities. Here, an advanced plasma-assisted etch strategy was used to fine tune the ozonation activity of monolayered graphene films by tailoring the defect types. Raman mapping indicated that the defects of the as-prepared monolayered graphene films were predominantly sp3, vacancy, and boundary-type defects, resp. The roles and contributions of these active defects in manipulating the oxidative potential of monolayered graphene films were revealed by quenching experiments, ESR results, and d. functional theory calculations The catalytic results showed that the monolayered graphene films with boundary-like defects exhibited the best catalytic performance toward the degradation of sulfamethoxazole. This work contributes new insights into the design of high-efficiency carbonaceous catalysts by structuring addnl. defective sites.

ACS Applied Materials & Interfaces published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C15H20O6, Product Details of C9H17NO.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

 

Khoukhi, Mostafa’s team published research in Tetrahedron Letters in 1986 | CAS: 106118-94-9

Tetrahedron Letters published new progress about active methylene alkylation azido iodoalkane; azido alkanoate chemoselective reduction; lactam azido active methylene cyclization; hydrazone alkylation azidoiodoalkane; azido ketone preparation cyclization; pyrroline; azidoiodoalkane primary amino protected electrophile. 106118-94-9 belongs to class piperidines, name is Methyl 2-oxopiperidine-3-carboxylate, and the molecular formula is C7H11NO3, Computed Properties of 106118-94-9.

Khoukhi, Mostafa published the artcileThe use of ω-iodo azides as primary protected electrophilic reagents. Alkylation of some carbanions derived from active methylene compounds and N,N-dimethylhydrazones, Computed Properties of 106118-94-9, the main research area is active methylene alkylation azido iodoalkane; azido alkanoate chemoselective reduction; lactam azido active methylene cyclization; hydrazone alkylation azidoiodoalkane; azido ketone preparation cyclization; pyrroline; azidoiodoalkane primary amino protected electrophile.

Carbanions generated from active methylene compounds RCHR1R2[R = H, Me, R1 = R2 = CO2R3(R3 = Me, Et); R = H, R1 = COMe, R2 = CO2Et, P(O)(OEt)2] were alkylated by primary amino protected electrophilic reagents, N3(CH2)nI (n = 2,3) to give N3(CH2)nCRR1R2 (I) in good yields. Chemoselective reduction of I (R = H, Me; R1 = R2 = CO2R3) with PPh3 gave lactams II (m = 1,2). Carbanions from MeCR4:NNMe2 (R4 = Me, cyclopropyl) reacted with N3CHR5CH2I (R5 = H, Bu) to give R5CH(N3)CH2CH2COR4, which cyclized to give pyrrolines II, on treatment with PPh3.

Tetrahedron Letters published new progress about active methylene alkylation azido iodoalkane; azido alkanoate chemoselective reduction; lactam azido active methylene cyclization; hydrazone alkylation azidoiodoalkane; azido ketone preparation cyclization; pyrroline; azidoiodoalkane primary amino protected electrophile. 106118-94-9 belongs to class piperidines, name is Methyl 2-oxopiperidine-3-carboxylate, and the molecular formula is C7H11NO3, Computed Properties of 106118-94-9.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

 

Mohammad, T.’s team published research in Journal of Labelled Compounds and Radiopharmaceuticals in 1986-07-31 | CAS: 27483-92-7

Journal of Labelled Compounds and Radiopharmaceuticals published new progress about thioridazine deuterated. 27483-92-7 belongs to class piperidines, name is 2-(Chloromethyl)-1-methylpiperidine hydrochloride, and the molecular formula is C7H15Cl2N, Recommanded Product: 2-(Chloromethyl)-1-methylpiperidine hydrochloride.

Mohammad, T. published the artcileSynthesis of deuterium-labeled thioridazine, Recommanded Product: 2-(Chloromethyl)-1-methylpiperidine hydrochloride, the main research area is thioridazine deuterated.

A 7-step synthetic route to (±)-thioridazine I (R = R1 = H) was developed starting from racemic Et 1-methyl-2-piperidinecarboxylate. LiAlD4 reduction of the starting and homologous esters allowed the incorporation of D in the 1- and/or 2-position(s) of the Et side chain of thioridazine. The isotopic purity of I (R = R1 = D; R = H, R1 = D; R = D, R1 = H) was >99%.

Journal of Labelled Compounds and Radiopharmaceuticals published new progress about thioridazine deuterated. 27483-92-7 belongs to class piperidines, name is 2-(Chloromethyl)-1-methylpiperidine hydrochloride, and the molecular formula is C7H15Cl2N, Recommanded Product: 2-(Chloromethyl)-1-methylpiperidine hydrochloride.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

 

Gawley, Robert E.’s team published research in Journal of Organic Chemistry in 1995-09-08 | CAS: 1690-74-0

Journal of Organic Chemistry published new progress about Alkylation. 1690-74-0 belongs to class piperidines, name is Methyl 1-methylpiperidine-2-carboxylate, and the molecular formula is C8H15NO2, Formula: C8H15NO2.

Gawley, Robert E. published the artcileAlkylation of 2-lithio-N-methylpiperidines and -pyrrolidines: scope, limitations, and stereochemistry, Formula: C8H15NO2, the main research area is alkylation lithio piperidine pyrrolidine stereochem.

The scope and limitations of the alkylation of racemic and nonracemic 2-lithiopiperidines and 2-lithiopyrrolidines, obtained by transmetalation of the corresponding stannanes, is reported. These organolithiums react with a variety of electrophiles to afford 2-substituted pyrrolidines and piperidines in excellent yield. With primary alkyl halides the reaction proceeds with net inversion of configuration at the metal-bearing carbon in the piperidines; in the pyrrolidines there is a mixture of inversion and retention, with the former predominating. With most carbonyl electrophiles (carbon dioxide, di-Me carbonate, Me chloroformate, pivaloyl chloride, benzaldehyde, and dialkyl ketones), retention is observed in both cases. Electrophiles such as benzophenone, benzyl bromide, and tert-Bu bromoacetate afford racemic coupling products. A mechanistic interpretation is presented.

Journal of Organic Chemistry published new progress about Alkylation. 1690-74-0 belongs to class piperidines, name is Methyl 1-methylpiperidine-2-carboxylate, and the molecular formula is C8H15NO2, Formula: C8H15NO2.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

 

Gomez, Elena’s team published research in Tetrahedron Letters in 2005-05-16 | CAS: 1690-74-0

Tetrahedron Letters published new progress about Reduction. 1690-74-0 belongs to class piperidines, name is Methyl 1-methylpiperidine-2-carboxylate, and the molecular formula is C8H15NO2, Synthetic Route of 1690-74-0.

Gomez, Elena published the artcile1,4-Dihydropicolinic acid derivatives: novel NADH analogues with an altered connectivity pattern, Synthetic Route of 1690-74-0, the main research area is alkylpyridinium reduction dithionite dihydropyridine NADH analog preparation.

Sodium dithionite reduction of α-substituted N-alkylpyridinium salts derived from picolinic acid derivatives afforded the corresponding 1,4-dihydropyridines with a new substitution pattern, in which the electron-withdrawing group is at the α-position. These compounds promote biomimetic reductions and are hence considered functional NADH analogs.

Tetrahedron Letters published new progress about Reduction. 1690-74-0 belongs to class piperidines, name is Methyl 1-methylpiperidine-2-carboxylate, and the molecular formula is C8H15NO2, Synthetic Route of 1690-74-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

 

Taguchi, Tanezo’s team published research in Chem. Pharm. Bull. (Tokyo) in 1965 | CAS: 27483-92-7

Chem. Pharm. Bull. (Tokyo) published new progress about Alcohols. 27483-92-7 belongs to class piperidines, name is 2-(Chloromethyl)-1-methylpiperidine hydrochloride, and the molecular formula is C7H15Cl2N, Quality Control of 27483-92-7.

Taguchi, Tanezo published the artcileHeteroalicyclic aminoalkanols. II. Reactions of DL-2-piperidylmethanol involving the formation of DL-1-azabicyclo[4.1.0]heptane, Quality Control of 27483-92-7, the main research area is .

2-Piperidylmethanol (I) (5 g.) in 5 cc. Et2O treated simultaneously with stirring at 0° with 6 g. BzCl in 20 cc. Et2O and 20 cc. aqueous NaOH and stirred 1 h. at room temperature yielded 7.2 g. 1-Bz derivative (II) of I, granules, m. 94-5° (Et2O). II (0.5 g.) in 20 cc. 2% aqueous HCl gave 0.53 g. benzoate (III) of I.HCl, rods, m. 243-4° (MeOH-EtOH). II with 2% HBr gave similarly 91% I.HBr, needles, m. 233-4° (decomposition) (EtOH). III.HCl (0.2 g.) stirred 0.5 h. with 10 cc. 5% aqueous NaOH yielded 0.15 g. II, granules, m. 74° (Et2O). I (1.15 g.) in 10 cc. Et2O treated dropwise with 9 cc. aqueous NaOH and then with 3 g. BzCl and stirred 3 h. yielded 2.8 g. 1-benzoyl-2-piperidylmethanol benzoate (IV), granules, m. 65-7° (Et2O-ligroine). II (0.5 g.) in 5 cc. C6H6 and 5 cc. 10% aqueous NaOH treated dropwise with stirring with 0.4 g. BzCl gave 0.66 g. IV, m. 65°. I ( 1 g.), 0.88 cc. BzH, and 10 cc. C6H6 refluxed 1 h. with 1 cc. AcOH with the azeotropic removal of H2O gave 1.3 g. V, b8 134-6°. V (0.5 g.) in 2 cc. CHCl3 treated dropwise with cooling and stirring with 0.4 g. Br in 2 cc. CHCl3 and then stirred with 2 cc. 10% aqueous NaOH gave 0.67 g. III.HBr, needles, m. 233° (EtOH). 2-ClCH2 analog (VI) (4 g.) of I.HCl and 2 g. CS(NH2)2 in 12 cc. EtOH refluxed 10 h. gave 2.5 g. 2-(2-pyridylmethyl)-2-thiopseudourea-2HCl (VIa.2HCl), needles, m. 182-4° (EtOH), and 0.8 g. VII.HCl, rods, m. 186-8° (BuOH). VIa.2HCl (0.2 g.) in 2 cc. BuOH refluxed 1 h. yielded 0.18 g. VII.HCl, needles, m. 186-8° (BuOH). VIa.2HCl (50 mg.) in 2 cc. EtOH treated successively with 0.57 cc. 2% alc. KOH, 41 mg. 2,4-(O2N)2C6H3Cl in 2 cc. EtOH, and 1.14 cc. 2% alc. KOH yielded 25 mg. 1-(2,4-dinitrophenylamidino)-2-(2,4-dinitrophenylthiomethyl)piper-idine, brownish yellow granules, m. 185-7° (decomposition). 1-Methyl-2-piperidylmethanol (VIII) (3 g.) in 30 cc. dry Et2O and then 1.8 cc. CS2 added dropwise with cooling and stirring to 0.46 g. powd. Na in 25 cc. dry Et2O, treated with 1.24 cc. MeI in 5 cc. dry Et2O, and worked up gave 3.1 g. Me 1-methyl-2-piperidylmethyl xanthate (IX), yellow oil; picrate, yellow needles, m. 124-6° (EtOH); IX.HCl m. 134-5° (EtOH-Et2O). The alk. hydrolysis of IX yielded VIII. VIII (4 g.) heated 0.5 h. at 130° yielded 3.5 g. S-(1-methyl-2-piperidylmethyl) S’-Me dithiolcarbonate (X), light yellow oil, b1 119-20°; picrate m. 164-5° (EtOH). VIII (7 g.) in 20 cc. dry CHCl3 refluxed 3 h. with 6 cc. SOCl2 gave 7.1 g. 2-ClCH2 analog (XI) of VIII.HCl, needles, m. 159-61° (Me2CO). XI.HCl (3 g.) and 1.23 g. CS(NH2)2 in 10 cc. EtOH refluxed 4 h. yielded 2.8 g. 2-(1-methyl-2-piperidylmethyl)-2-thiopseudourea-2HCl (XII.2HCl), needles, m. 192-3° (BuOH). XII.2HCl (0.7 g.) heated 1 h. on the water bath with 5 cc. 2N NaOH and treated with a stream of air gave 0.68 g. bis(1-methyl-2-piperidylmethyl) disulfide (XIII); dipicrate m. 153-5° (MeOH). X (1 g.) and 40 cc. 5% alc. NaOH heated I hr. on the water bath, treated dropwise with 10% alc. HCl (EtSH evolved), and the crude product treated in aqueous K2CO3 with air overnight yielded 0.8 g. XIII picrate, m. 151-4° (MeOH). VIII.MeI (8 g.) and Ag2O from 12 g. AgNO3 and 20 cc. 10N NaOH stirred 5 h., filtered, and evaporated, and the residue heated 3 h. at 100° in vacuo under N gave 1 g. VIII and 1.1 g. Me2N(CH2)5CHO, b3 168-70°; picrate m. 146-8° (H2O). I (6 g.) added with cooling to 5 cc. concentrated H2SO4 and heated gradually to 240° yielded 7.4 g. 2-HO3SOCH2 analog (XIV) of I, rods, m. 262-3° (decomposition) (MeOH). XIV (6 g.) in 40 cc. H2O and 100 cc. 10% aqueous NaOH distilled and the distillate treated with solid KOH gave 0.2 g. XV, b80 65°, which polymerized completely within several hrs., even under N; XV picrate m. 151-2° (Et2O-AcOEt). XV (0.1 g.) in Et2O stirred 1 h. and treated with K2CO3, and the basic product treated with picric acid gave the picrate of I, m. 115° (EtOH-Et2O). XV (0.1 g.) in Et2O treated with dry HCl and kept overnight gave VI.HCl, m. 187-8°. XV (0.1 g.) in Et2O treated overnight with 0.1 g. MeBr in Et2O gave 0.16 g. 2-bromomethyl-1,1-dimethylpiperidinium bromide (XVI), granules, m. 230° (EtOH). XV (0.14 g.), 0.1 g. CS(NH2)2, 1.32 cc. N HCl, and 2 cc. H2O stirred a few min., treated with an addnl. 1.32 cc. N HCl, and stirred 1 h., and the crude product refluxed 1 h. in BuOH gave VII isolated as the picrate, m. 1523° (H2O). I (3 g.) in 30 cc. 48% aqueous HBr refluxed 10 h. yielded 4.1 g. 2-bromomethylpiperidine-HBr (XVII.HBr), needles, m. 188-90° (EtOH). XVII.HBr (0.5 g.) in 10 cc. Et2O treated overnight with 20 cc. 10% MeBr-Et2O gave 0.57 g. XVI, granules, m. 233-4° (decomposition) (EtOH).

Chem. Pharm. Bull. (Tokyo) published new progress about Alcohols. 27483-92-7 belongs to class piperidines, name is 2-(Chloromethyl)-1-methylpiperidine hydrochloride, and the molecular formula is C7H15Cl2N, Quality Control of 27483-92-7.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

 

Kasuga, Seiki’s team published research in Chemical & Pharmaceutical Bulletin in 1965 | CAS: 27483-92-7

Chemical & Pharmaceutical Bulletin published new progress about Alcohols. 27483-92-7 belongs to class piperidines, name is 2-(Chloromethyl)-1-methylpiperidine hydrochloride, and the molecular formula is C7H15Cl2N, Computed Properties of 27483-92-7.

Kasuga, Seiki published the artcileHeteroalicyclic aminoalkanols. I. Syntheses of DL-2-piperidylmethanol and meso-cis-2,6-bis(hydroxymethyl)piperidine and reactions of intermediates, Computed Properties of 27483-92-7, the main research area is ALCOHOLS; CHEMISTRY, PHARMACEUTICAL; EXPERIMENTAL LAB STUDY; PIPERIDINES; PYRIDINES.

2-Acetoxymethyl-6-methyl- pyridine 1-oxide (I) (20 g.) in 100 cc. 48% aqueous HBr refluxed 4 h. yielded 27.1 g. 2-BrCH2 analog (II) of I.HBr, colorless rods, m. 123-4° (Me2CO). 2,6-Bis(acetoxymethyl)pyridine 1-oxide (10 g.) yielded similarly 10.5 g. 2,6-bis(bromomethyl)pyridine 1-oxide (III), granules, m. 153-5° (MeOH). 2-Bromomethylpyridine 1-oxide-HBr (IV.HBr) (5 g.) treated with alkali, and the free IV heated 2.5 h. on the water bath with 1.2 cc. CS(NH2)2 in 100 cc. EtOH yielded 3.5 g. 2-(2-pyridylmethyl)-2-thiopseudourea N-oxide-HBr (V.HBr), rods, m. 184-5° (decomposition) (MeOH). II yielded similarly the 2-(6-methyl-2-pyridylmethyl) analog (VI) of V.HBr, rods, m. 191-2° (EtOH). III gave similarly 65% VII.2HBr, granules, m. 203-5° (decomposition). Na (0.34 g.) in 23 cc. absolute EtOH treated with dry H2S until alk. and then with IV in EtOH from 5 g. IV.HBr, and the resulting gummy product dissolved in 5 cc. 4N alc. HCl with warming, filtered from some bis-(1-oxo-2-pyridylmethyl) disulfide-2HCl (VIII.2HCl), and worked up yielded 2-pyridylmethanethiol 1-oxide-HCl (IX.HCl), rods, m. 114-15° (Me2CO). II gave similarly the 6-Me derivative (X) of IX.HCl, 21%, rods, m. 133-4° (EtOH), and some 6,6′-dimethyl derivative (XI) of VIII, m. 160-4°. VI (0.2 g.) in 0.6 cc. 2N NaOH heated 2 h. on the water bath under N, cooled, and acidified with alc. HCl yielded 0.02 g. X.2HCl, m. 132-3° (Et2O-EtOH). IV from 3 g. IV.HBr heated 2 h. on the water bath with 5 cc. H2O containing 1.34 g. Na2S.9H2O yielded 0.5 g. bis(1-oxo-2-pyridylmethyl) sulfide (XII), yellow rods, m. 1745° (decomposition); picrate m. 148° (EtOH). II gave similarly 35% 6,6′-dimethyl derivative of XII, light yellow rods, m. 121-2° (AcOEt); XI.2HCl, granules, m. 163-4° (EtOH). Na2S.9H2O (1.34 g.) and 0.23 g. S in 10 cc. H2O heated 2 h. on the water bath with IV from 3 g. IV.HBr, and the gummy product treated with 3 cc. 4N alc. HCl yielded 0.3 g. VlII.2HCl, rods, m. 1623° (decomposition) (MeOH); picrate m. 139-40° (EtOH). IX in EtOH aerated overnight gave VIII which was converted to the picrate, m. 135-9°. II treated with Na2S yielded 28% XI.2HCl, m. 192-3° (decomposition). X oxidized with air and treated with HCl gave 38.5% XI.2HCl, m. 192-3° (decomposition). IV from 2.8 g. IV.HBr stirred 2 h. with 40 cc. H2O containing 2.7 g. EtSNa yielded 0.5 g. oily, yellowish 2-ethylthiomethylpyridine 1-oxide (XIII), b6, 134-7°; picrolonate, m. 137° (EtOH). II gave similarly 39% yellow, oily 6-Me derivative of XIII, b3 143-6°; picrolonate m. 120.5-21° (EtOH). II (1 g.) refluxed 4 h. with 5 cc. Ac2O yielded 0.5 g. pink oil, b2 90-115° which refluxed 4 h. with 10 cc. 47% aqueous HBr gave 0.28 g. III.HBr, m. 208-10° (decomposition) (EtOH); the filtrate treated with 2,4-(O2N)2C6H3-NHNH2 in aqueous H3PO4 yielded 6-methylpyridine-2-carboxaldehyde 2,4-dinitrophenylhydrazone (XIV), m. 231-3° (decomposition). X in Ac2O refluxed 3 h. under N yielded 21% 6-methyl-2-pyridylmethanethiol acetate (XV), yellow oil, b5 112-14°; picrolonate m. 164-5° (decomposition) (EtOH). 2-Ethylthiomethyl-6-methylpyridine 1-oxide (3 g.) in 9 cc. Ac2O refluxed 4 h. yielded 3.4 g. 2-(acetoxy)(ethylthio)methyl-6-methylpyridine (XVI), pink oil, b5 143-4°; picrate m. 105-7° (aqueous EtOH). XVI (1 g.) and 20 cc. 20% aqueous HCl refluxed 10 h. under N (EtSH evolved) yielded 0.46 g. oil, b12 77-8°, which gave XIV, m. 230°. IV.HBr (1 g.) in 6 cc. 2N NaOH kept 1 h. at room temperature gave 0.41 g. bis-(1-oxo-2-pyridylmethyl) oxide H2O (XVII.H2O), needles, m. 128-9° (AcOEt); picrate m. 192-3° (EtOH). Bis(2-pyridylmethyl) oxide (XVIII) (0.2 g.), 2 cc. AcOH, and 0.4 cc. 30% H2O2 heated 12 h. at 70-80° gave 0.1 g. XVII.H2O, m. 127°. XVII.H2O (0.3 g.) in 15 cc. 48% HBr refluxed 7 h. yielded IV, isolated as the picrate, m. 129-30°. XVII.H2O (0.4 g.) in 30 cc. CHCl3 heated 1 h. on the water bath with 0.3 cc. PCl3 and basified with aqueous K2CO3 gave 0.23 g. oily XVIII, b4 146-8°; picrate m. 197-8° (decomposition) (EtOH). 2-Pyridylmethanol (XIX) (2 g.) in 10 cc. xylene treated with stirring and cooling with 5.4 g. concentrated H2SO4 and heated 5 h. at 160-70° with the azeotropic removal of H2O gave 1.6 g. unreacted XIX, b8 100-5°, and 0.22 g. XVIII, b3 145-8°. 2-Bromomethylpyridine-HBr (XX.HBr) (1 g.) stirred 5 h. with 10 cc. 2N NaOH gave 0.21 g. XIX, b4 74-80°, and 0.23 g. XVIII, b4 80-124°. II treated with PCl3 gave 82.3% bis(1-oxo-6-methyl-2-pyridylmethyl) oxide-0.5H2O (XXI.-0.5H2O), needles, m. 175-7° (MeOH); picrate m. 174-5° (EtOH). 6,6′-Dimethyl derivative (XXII) of XVIII in xylene refluxed with concentrated H2SO4 gave 78.5% XXI.0.5H2O. 6-Me derivative (XXIII) of XIX gave similarly unreacted XXIII and 33.8% XXII, b4 150-5°, which yielded a dipicrate, m. 210-12° (decomposition). The 6-Me derivative of XX stirred 5 h. with 2N NaOH yielded 63.2% XXII, m. 75-6° (H2O). XVII.H2O (5 g.) and 30 cc. Ac2O refluxed 4 h. yielded 1.4 g. picolinecarboxaldehyde diacetate, b3 118-23° [picrate m. 146-7° (EtOH)], and 2.15 g. 2-pyridylmethyl picolinate (XXIV), b0.05 155-7°, m. 52-3° (ligroine). Picolinic acid (1.6 g.) in 3 cc. C6H6 treated with cooling and stirring with 6 cc. concentrated H2SO4 and 1.1 g. XIX, and the mixture refluxed with the overhead removal of H2O-C6H6 azeotrope and the dropwise addition of C6H6 during 6 h., poured onto ice, and basified with aqueous K2CO3 yielded 0.5 g. unreacted XIX and 0.26 g. XXIV, m. 52-3° (ligroine). XIX (50 g.) in 50 cc. EtOH hydrogenated 7 h. with stirring at 80° and 200 atm. initial pressure over 50 cc. Raney Ni W-2 yielded 47.8 g. 2-piperidylmethanol, b13 108°; picrate m. 133-5° (EtOH). Di-Me meso-cis-2,6-piperidinedicarboxylate (1 g.), 0.5 g. LiAlH4, and 40 cc. Et2O refluxed 3 h. yielded 1.5 g. meso-cis-2,6-bis(hydroxymethyl)piperidine (XXV), plates, m. 130-1° (AcOEt). 2,6-Bis(hydroxymethyl)pyridine (4 g.) in 20 cc. EtOH hydrogenated over 10 cc. Raney Ni yielded 3.4 g. XXV. Di-Me 2,6-pyridinedicarboxylate (3.5 g.) in 35 cc. MeOH hydrogenated over 15 cc. Raney Ni gave 2.2 g. XXV, plates, m. 128-30°.

Chemical & Pharmaceutical Bulletin published new progress about Alcohols. 27483-92-7 belongs to class piperidines, name is 2-(Chloromethyl)-1-methylpiperidine hydrochloride, and the molecular formula is C7H15Cl2N, Computed Properties of 27483-92-7.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

 

Gawley, Robert E.’s team published research in Journal of the American Chemical Society in 1993-08-11 | CAS: 1690-74-0

Journal of the American Chemical Society published new progress about Configuration. 1690-74-0 belongs to class piperidines, name is Methyl 1-methylpiperidine-2-carboxylate, and the molecular formula is C8H15NO2, Computed Properties of 1690-74-0.

Gawley, Robert E. published the artcile2-Lithio-N-methylpiperidine and 2-lithio-N-methylpyrrolidine: configurationally and chemically stable unchelated α-aminoorganolithiums, Computed Properties of 1690-74-0, the main research area is lithiomethylpiperidine preparation configurational stability; lithiomethylpyrrolidine preparation configurational stability; piperidine lithiomethyl preparation configurational stability; pyrrolidine lithiomethyl preparation configurational stability.

Enantiomerically pure 2-lithio-N-methylpiperidine and enantiomerically enriched 2-lithio-N-methylpyrrolidine (94% ee) have been made by tin-lithium exchange and evaluated for their chem. and configurational stability. Both show remarkable stability in the presence of TMEDA, resisting racemization at temperatures up to -40°.

Journal of the American Chemical Society published new progress about Configuration. 1690-74-0 belongs to class piperidines, name is Methyl 1-methylpiperidine-2-carboxylate, and the molecular formula is C8H15NO2, Computed Properties of 1690-74-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

 

Anderson, Fiona M.’s team published research in Anti-Cancer Drug Design in 2000-04-30 | CAS: 27483-92-7

Anti-Cancer Drug Design published new progress about Alkylating agents. 27483-92-7 belongs to class piperidines, name is 2-(Chloromethyl)-1-methylpiperidine hydrochloride, and the molecular formula is C7H15Cl2N, COA of Formula: C7H15Cl2N.

Anderson, Fiona M. published the artcileSynthesis of new homochiral bispyrrolidines as potential DNA cross-linking antitumor agents, COA of Formula: C7H15Cl2N, the main research area is structure activity antitumor bispyrrolidine DNA crosslinking.

We are seeking to develop more effective bifunctional alkylating agents as antitumor agents. We previously synthesized conformationally restricted nitrogen mustards containing one piperidine ring, then bispiperidine derivatives were designed and prepared with varying lengths of carbon chain between the two rings and structure-activity relationships in these systems were studied. A bispiperidine with the shortest bridge of two carbon atoms was the most reactive bifunctional alkylating agent. In order to extend this work and investigate the effects of a change in the size of the heterocyclic systems, new bispyrrolidine salts 17-23 with chloromethyl groups at the 2-positions and a bridge between the two nitrogen atoms of 2-8 carbon atoms were synthesized from L-proline so that only the LL-enantiomers were produced. The free bases were designed to be bifunctional alkylating agents via aziridinium ion formation with different distances between the two alkylating sites. All of the bispyrrolidines were efficient cross-linkers of naked DNA apart from those with three-carbon (18) and four-carbon (19) bridges, in contrast to the results with the bispiperidines. A piperazine derivative 24 with two potential alkylating sites was also shown to be an efficient cross-linker, as was an alicyclic compound 25 with six carbon atoms between the two alkylating sites. Compounds 26 and 30 with an extra carbon atom between the nitrogen and the leaving group were not cross-linkers, as expected if aziridinium ion formation is crucial for crosslinking ability. The preformed aziridine 27 with a further alkylating site was an efficient cross-linker. Compounds 28-29 with only one potential alkylating center were not cross-linkers of DNA. None of the compounds, however, produced significant cytotoxicity in human tumor cells in vitro.

Anti-Cancer Drug Design published new progress about Alkylating agents. 27483-92-7 belongs to class piperidines, name is 2-(Chloromethyl)-1-methylpiperidine hydrochloride, and the molecular formula is C7H15Cl2N, COA of Formula: C7H15Cl2N.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem